Semisynthesis and antiproliferative evaluation of a series of 3′-aminoflavones

A series of 3′-aminoflavones 5,6,7,8-tetra- or 5,7-dioxygenated on the A-ring was synthesized from tangeretin or naringin, two natural Citrus flavonoids. These flavones were evaluated for antiproliferative activity, activation of apoptosis, and inhibition of tubulin assembly. The most antiproliferative flavones exhibit a common 5-hydroxy-6,7,8-trimethoxy substitution pattern on the A-ring.

Graphical abstractA series of 3′-aminoflavones 5,6,7,8-tetra or 5,7-dioxygenated on the A-ring was synthesized from tangeretin or naringin, two natural Citrus flavonoids, then evaluated for their antiproliferative and proapoptotic activities, and for the inhibition of tubulin assembly.Figure optionsDownload full-size imageDownload as PowerPoint slide